Triethylamine → N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide

HRID 351735

反応式

HRID 351735 の反応式
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[C:25]1([C:31]([OH:35])([C:33]#[CH:34])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl.[Cu]I>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:34]#[C:33][C:31]([OH:35])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:32])[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 129913181-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

生成物 1

HCID 10161154N-Isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro [1,8]naphthyridin-4-one-3-carboxamide

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of N-isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 4 of EXAMPLE 1, 2-phenyl-3-butyn-2-ol (2 eq), triethylamine (1.66 eq), bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq), and copper(I) iodide (5 mg/mmol) in DMF (20 ml/mmol) was heated at 85° C. for 18 hours. After cooling to room temperature, the resulting mixture was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with 20% ether in methylene chloride. The purified product was stirred in ether at room temperature for 3 hours and filtered to afford the title compound as a white solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe resulting mixture was quenched with saturated aqueous ammonium chloride solution
  3. custompartitioned between ethyl acetate and water
  4. customThe crude product from the organic phase was chromatographed on silica gel eluting with 20% ether in methylene chloride
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-dd67d90dc91049d59b4870fc9e136467
出典データセット
uspto-grants-2004_06
特許番号
US06743802B2

関連ノート

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